US3806472A - Perfume composition containing hydrogenated indane derivative - Google Patents

Perfume composition containing hydrogenated indane derivative Download PDF

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US3806472A
US3806472A US00286994A US28699472A US3806472A US 3806472 A US3806472 A US 3806472A US 00286994 A US00286994 A US 00286994A US 28699472 A US28699472 A US 28699472A US 3806472 A US3806472 A US 3806472A
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pentamethylindane
perfume composition
perfume
derivative
composition containing
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US00286994A
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J Hall
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International Flavors and Fragrances Inc
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International Flavors and Fragrances Inc
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Priority to US851076A priority Critical patent/US3636165A/en
Priority to US00851049A priority patent/US3773836A/en
Priority to US851086A priority patent/US3636176A/en
Priority to US851090A priority patent/US3647826A/en
Priority to US851048A priority patent/US3681464A/en
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Priority to US00286994A priority patent/US3806472A/en
Priority claimed from US00325676A external-priority patent/US3839368A/en
Priority claimed from US00325677A external-priority patent/US3816350A/en
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0084—Antioxidants; Free-radical scavengers
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
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    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
    • C07C13/465—Indenes; Completely or partially hydrogenated indenes
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    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
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    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
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    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
    • C07C35/32—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.3.0) system, e.g. indenols
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of SO3H groups or a derivative thereof
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
    • C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/427—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/443—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
    • C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/633—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
    • C07C5/11—Partial hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B9/00—Esters or ester-salts of leuco compounds of vat dyestuffs
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
    • C11D9/442—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/01—Aerosol hair preparation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/02—Resin hair settings

Definitions

  • dashed lines represent single or double bonds, no more than two of the dashed lines represent double bonds and, when two double bonds are present, such bonds are unconjugated.
  • fragrance materials having persistent amber woody odors with satisfactory overtones or qualities. While many natural products have amber woody fragrances, the more desirable of these are frequently in short supply and hence difficult to obtain and expensive. Moreover, it is also most desirable that such amber woody fragrance character have good persistence so that the substances can be used in quality formulations for perfume or other olfactory compositions. Such materials should also possess good blending qualities so that they are useful in preparing perfume compositions.
  • the present invention provides a novel hydrogenated indane derivative, 4,5-dihydro-1,1,2,3,3-pentamethylindane, having the formula:
  • This substance has a strong, persistent, woody amber odor with various elegant piney overtones.
  • the present invention also provides novel perfume and fragrance compositions containing such hydrogenated indane, and processes for producing such indane are also disclosed herein.
  • the invention also contemplates 5,7a-dihydro-1,1,2,3,3- pentamethylindane having the formula:
  • Such isomeric dihydroindanes are also useful in the formulation of olfactory compositions.
  • the present invention further contemplates 4,5,6,7- tetrahydro 1,1,2,3,3 pentamethylindane having the formula:
  • indane derivatives according to this invention can exist in several stereoisomeric forms, and it is contemplated that the formula given herein includes the several isomeric forms.
  • a convenient starting material according to the present invention is pentamethylindane.
  • the pentamethylindane is hydrogenated to provide the tet-rahydro derivative and/or the hexahydro derivative as the first step in the synthesis.
  • the bridge double bond of the tetrahydro derivative is then oxidized with a suitable agent to obtain the epoxyindane.
  • the hexahydro derivative can be dehydrogenated if desired to obtain the 1,1,2,3,3-pentamethylindane for recycling or for other syntheses. Such dehydrogenation can also provide a useful fragrance material.
  • the hydrogenation is carried out under controlled conditions to add two moles of hydrogen to each mole of the indane.
  • metallic catalysts such as Raney nickel or noble metals such as palladium, rhodium, and the like.
  • Such catalysts can be supported on carriers such as carbon and the like.
  • the hydrogenation is carried out at substantially superatmospheric pressures of from 50 to 200 atmospheres, and is preferably carried out at 60 to atmospheres.
  • the reaction is desirably carried out at temperatures in excess of 100 C. up to 225 C., and a preferred temperature range is to C.
  • the hexahydro derivative is obtained under these same conditions through the addition of three moles of hydrogen.
  • the 4,5,6,7-tetrahydropentamethylindane so obtained is oxidized to provide the epoxy oxygen substituent on the 3a,7a bridge carbon atoms.
  • the oxidation is carried out with an oxidizer such as percarboxylic acid.
  • peracids such as peracetic, perpropionic, perbenzoic, perphthalic, and the like are used.
  • lower aliphatic percarboxylic acids are used.
  • peracetic acid can be used, although a combination of acetic anhydride and hydrogen peroxide is equivalent.
  • the amount of percarboxylic acid used should be about stoichiometric, although slight excesses up to about ten molar percent can be used.
  • An alkali metal salt of the corresponding carboxylic acid e.g., sodium acetate for-peracetic acid, is desirably used to butfer'the reaction mixture.
  • the dihydropentamethylindane is formed by refluxing the epoxide as prepared 'above with sulfuric acid or a sulfonic acid agent such as benzenesulfonic acid, ptoluenesulfonic acid, methanesulfonic acid, and the like or a Lewis acid such as boron trifluoride, boron trifluorideetherate, and the like.
  • sulfuric acid or a sulfonic acid agent such as benzenesulfonic acid, ptoluenesulfonic acid, methanesulfonic acid, and the like or a Lewis acid such as boron trifluoride, boron trifluorideetherate, and the like.
  • a sulfonic acid agent such as benzenesulfonic acid, ptoluenesulfonic acid, methanesulfonic acid, and the like or a Lewis acid such as boron trifluoride, boron
  • This reaction can be carriedv out at pressures above or below atmospheric, but atmospheric pressure is desired to minimize ebullition' of any reaction vehicle and provide an acceptable reaction rate, while maintaining control overv the-reaction.
  • the temperatures used are in the range of 15 to 120 C., depending upon the catalyst used.
  • reaction is suitably carried out in the presence of a vehicle, and solvents for the epoxide and agent are desirable.
  • vehicle include aromatic hydrocarbons such as benzene, toluene, xylene, and the like, and benzene is a preferred vehicle.
  • dihydro derivatives can be produced directly from the pentamethylindane or by isomerization of the 4, -dihydro derivative described above.
  • the .pentamethylindane can be treatedwith an alkali metal, desirably lithium, in liquid or gaseous ammonia also to provide the 5,7a-dihydro derivatives.
  • Such treatment is carried out at temperatures of from about -40 C. to about 25 C.
  • At the lower temperature atmosperic or slightly subatmospheric pressures can be used. With liquid ammonia at the higher temperatures, superatmospheric pressures up to about five atmospheres are used. Reaction times of from 15 minutes to four hours can be used.
  • the conjugated 3a,4 dihydro derivative is produced from the non-conjugated material by treatment with an alkali metal, preferably lithium, in an alkylamine, desirably a lower alkylamine such as ethylamine and the like. While it can be conducted at subor superatmospheric pressures, the reaction is desirably carried out at atmospheric pressures. Temperatures of to 17 C. are used, and the time is from 30 minutes to four hours.
  • an alkali metal preferably lithium
  • an alkylamine desirably a lower alkylamine such as ethylamine and the like. While it can be conducted at subor superatmospheric pressures, the reaction is desirably carried out at atmospheric pressures. Temperatures of to 17 C. are used, and the time is from 30 minutes to four hours.
  • hydrocarbons produced according to'the above reaction schemes can be separated from the vehicle and any unreacted materials or unwanted by-pr'oducts rcmoved by conventional means including washing, distillation, extraction, preparative chromatography, and the like. It is preferred to fractionally distill the washed reaction product under a relatively high vacuum so as to obtain a pure product. Product purities of 80% vare readily obtained, and much higher purities can also be provided by suitable treatment. All parts, proportions, percentages and ratios herein are by Weight unless otherwise indicated.
  • the dihydropentamethylindanes of this invention are useful as fragrances. They can be used to contribute a woody amber fragrance. As olfactory agents the indane derivatives of this invention can be formulated into or used as components of a perfume composition.
  • perfume composition is used herein to mean a mixture of organic compounds, including, for example, alcohols, aldehydes, ketones, esters, and frequently hydrocarbons which are admixed so that the combined'odors of the individual components produce a pleasant'or desired fragrance.
  • perfume compositions ii'sually “contain: (a) the main note. or the bouquet or foundationstone of the composition; (b) modifiers which round-01f and accompany the main note; (0) fixativeswhich include odorous substances which lend a particular note to the perfume throughout all stages of evaporation, and substances which retard evaporation; and (d) top-notes which are usually low-boiling fresh-smelling materials.
  • perfume compositions the individual component will contribute its particular olfactory characteristics, but the overall effect of the perfume composition will be the sum of the effect of each ingredient.
  • the individual compounds of this invention, or mixtures thereof, can
  • the indane derivatives of this invention can be used alone or in a perfumecomposition as an olfactory component in detergents and soaps; space deodorants; perfumes; colognes; bath preparations such as bath oil-and bath salts; hair preparations such as lacquers, brilliantines, pomades, and shampoosg cosmetic preparations such as creams, deodorants, hand lotions, and sun screens; powders such as talcs, dusting powders, face powder, and the like.
  • the perfume composition can contain, a vehicle or carrier for the other ingredients.
  • the vehicle can be a liquid such as alcohol, glycol, or the like.
  • the carrier can be an absorbent solid such as a gum or components for encapsulating the composition.
  • the pentamethylindane derivatives according to this invention can be used to enhance, modify, or supplement the fragrance properties of natural or synthetic fragrance compositions.
  • such preferred dihydroindanes can be used in fragrance compositions .for addition to perfume compositions or directly to products such as soap, detergents, cosmetics, and the like.
  • the fragrance compositions so prepared do not entirely provide the olfactory properties to the finished perfume or other article, but they, do furnish a substantial part of the overallfragrance impression.
  • Enough hydrogen is fed into the autoclave to raise the pressure to 1,000 p.s.i.-g.
  • the hydrogen feed is continuous until two moles of hydrogen are absorbed, and:the' auto.- clave is heated to a temperature in the range-of -185 9 C. over a period of about 8 hours until an amount of. H equalv to 10% in excess of theory is absorbed.
  • the pressure in the autoclave is maintained at 1,500 p.s.i.g.
  • the 1,641 g. of crude product removed from the autoe clave is distilled on a 12-inch Goodloe column after being mixed with 10.0 g. of Primol mineral oil. The distillate is recovered in two fractions.
  • Fraction 1 Distills at a temperature of 80 C. and 4.0 mm. Hg to provide 401 g. of 4,5,6,7-tetrahydro-1,1,2,3,3- pentamethylindane.
  • the solvent is stripped off leaving a crude product weighing 208 g.
  • the crude epoxy product is distilled on.,.,
  • This material has a fine woody, amber-tobacco aroma. with an elegant piney note.
  • the perfume composition comprises the following ingredients:
  • EXAMPLE V Preparation of a cosmetic powder composition
  • a cosmetic powder is prepared by mixing 100 grams of talcum powder with 0.25 gram of the dihydroindane obtained from the process of Example H in a ball mill.
  • the cosmetic powder has a desirable woody-amber odor.
  • EXAMPLE VI Liquid detergent Concentrated liquid detergents with a woody-amber, piney odor are prepared containing 0.1%, 0.15%, and 0.20% of the dihydroindane produced in Example II. They are prepared b adding and homogeneously mixing the appropriate quantity of the compound to Ultra Chemical Companys P-87 liquid detergent.
  • EXAMPLE VII A 100-ml. reaction flask is fitted with a mechanical stirrer, condenser, and thermometer, and 2.5 g. of hexahydropentamethylindane as produced in Example I and 2.5 g. of palladium on carbon catalyst containing 10% palladium are charged to the flask. The flask contents are brought to 234 C. and refluxed at that temperature for two hours until no further reaction is evident.
  • the catalyst is then filtered off and the filtrate is analyzed.
  • the product obtained is largely l,1,2,3,3-pentamethylindane.
  • EXAMPLE IX An aliquot of the dihydroindane derivative produced in Example VIII is treated by dissolving lithium in ethylamine until the blue color disappears from the mass and then adding the dihydro material with stirring and continuing the stirring under reflux for one hour.
  • the ethylamine is evaporated, water is added, and the aqueous mixture is extracted with hexane.
  • the product is found to contain 321,4 dihydro 1,1,2,3,3 penta-rnethylindane. This has an amber woody fragrance character suitable for incorporation into perfume compositions such as that set forth in Example III.
  • a perfume composition containing as anessential ingredient a fragrance imparting amount of at least one indane derivative selected from the group consisting of 5,7a dihydro 1,1,2,3,3 pentarnethylindane; '3a, 4-dihydro 1,1,2,3,3 pentamethylindane; 4,5,6,' l'- tetrahy- 8 dro-l,1,2,3,3-pentamethylindane; and .hexahydro-1,l,2,3, 3-pentamethylindane and an auxiliary perfume ingredient.

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Abstract

A PERFUME COMPOSITION CONTAINING A HYDROGENATED INDANE DERIVATIVE HAVING THE FORMULA:

1,1,2,3,3-PENTA(CH3-)HEXAHYDROINDAN WITH DASHED LINES

BETWEEN THE 3A AND 4, 4 AND 5, 5 AND 6, 7 AND 7A, AND

7A AND 3A POSITIONS

WHEREN THE DASHED LINES REPRESENT SINGLE OR DOUBLE BONDS, NO MORE THAN TWO OF THE DASHED LINES REPRESENT DOUBLE BONDS AND, WHEN TWO DOUBLE BONDS ARE PRESENT, SUCJ BONDS ARE UNCONJUGATED.

Description

United States Patent 3,806,472 PERFUME COMPOSITION CONTAINING HYDRO- GENATED INDANE DERIVATIVE John B. Hall, Rumson, NJ., assignor to International Flavors & Fragrances Inc., New York, NY.
No Drawing. Application Feb. 16, 1971, Ser. No. 115,834, now US. Patent No. 3,751,500, which is a division of Ser. No. 851,086, Aug. 18, 1969, now Patent No. 3,636,176. Divided and this application Sept. 7, 1972, Ser. No. 286,994
Int. Cl. Cllb 9/00; A611: 7/00 US. Cl. 252-522 1 Claim ABSTRACT OF THE DISCLOSURE A perfume composition containing a hydrogenated indane derivative having the formula:
wherein the dashed lines represent single or double bonds, no more than two of the dashed lines represent double bonds and, when two double bonds are present, such bonds are unconjugated.
This application is a division of applicants copending parent application Ser. No. 115,834, filed on Feb. 16, 1971, now U.S. Pat. 8,751,500 which, in turn, is a division of Ser. No. 851,086, filed on Aug. 18, 1969, now US. Pat. 3,636,176.
BACKGROUND OF THE INVENTION There is a continuing need for fragrance materials having persistent amber woody odors with satisfactory overtones or qualities. While many natural products have amber woody fragrances, the more desirable of these are frequently in short supply and hence difficult to obtain and expensive. Moreover, it is also most desirable that such amber woody fragrance character have good persistence so that the substances can be used in quality formulations for perfume or other olfactory compositions. Such materials should also possess good blending qualities so that they are useful in preparing perfume compositions.
THE INVENTION Briefly, the present invention provides a novel hydrogenated indane derivative, 4,5-dihydro-1,1,2,3,3-pentamethylindane, having the formula:
This substance has a strong, persistent, woody amber odor with various elegant piney overtones. Thus the present invention also provides novel perfume and fragrance compositions containing such hydrogenated indane, and processes for producing such indane are also disclosed herein.
The invention also contemplates 5,7a-dihydro-1,1,2,3,3- pentamethylindane having the formula:
and
3,806,472 Patented Apr. 23, 1974 3a,4-dihydro-1,1,2,3,3-pentamethylindane having the formula:
Such isomeric dihydroindanes are also useful in the formulation of olfactory compositions.
The present invention further contemplates 4,5,6,7- tetrahydro 1,1,2,3,3 pentamethylindane having the formula:
and hexahydro 1,1,2,-3,'3 pentamethylindane having the formula:
These materials are useful in preparing a variety of perfume compositions, as taught hereinafter.
It will be appreciated by those skilled in the art from the present disclosure that the indane derivatives according to this invention can exist in several stereoisomeric forms, and it is contemplated that the formula given herein includes the several isomeric forms.
A convenient starting material according to the present invention is pentamethylindane. In one aspect, the pentamethylindane is hydrogenated to provide the tet-rahydro derivative and/or the hexahydro derivative as the first step in the synthesis. In this synthesis the bridge double bond of the tetrahydro derivative is then oxidized with a suitable agent to obtain the epoxyindane.
The hexahydro derivative can be dehydrogenated if desired to obtain the 1,1,2,3,3-pentamethylindane for recycling or for other syntheses. Such dehydrogenation can also provide a useful fragrance material.
For the tetrahydro derivative, the hydrogenation is carried out under controlled conditions to add two moles of hydrogen to each mole of the indane. It is preferred to use metallic catalysts such as Raney nickel or noble metals such as palladium, rhodium, and the like. Such catalysts can be supported on carriers such as carbon and the like.
The hydrogenation is carried out at substantially superatmospheric pressures of from 50 to 200 atmospheres, and is preferably carried out at 60 to atmospheres. The reaction is desirably carried out at temperatures in excess of 100 C. up to 225 C., and a preferred temperature range is to C. The hexahydro derivative is obtained under these same conditions through the addition of three moles of hydrogen.
In one aspect, the 4,5,6,7-tetrahydropentamethylindane so obtained is oxidized to provide the epoxy oxygen substituent on the 3a,7a bridge carbon atoms. The oxidation is carried out with an oxidizer such as percarboxylic acid. Thus, peracids such as peracetic, perpropionic, perbenzoic, perphthalic, and the like are used. In preferred embodiments of the process, lower aliphatic percarboxylic acids are used. Thus, peracetic acid can be used, although a combination of acetic anhydride and hydrogen peroxide is equivalent. The amount of percarboxylic acid used should be about stoichiometric, although slight excesses up to about ten molar percent can be used. An alkali metal salt of the corresponding carboxylic acid, e.g., sodium acetate for-peracetic acid, is desirably used to butfer'the reaction mixture.
The dihydropentamethylindane is formed by refluxing the epoxide as prepared 'above with sulfuric acid or a sulfonic acid agent such as benzenesulfonic acid, ptoluenesulfonic acid, methanesulfonic acid, and the like or a Lewis acid such as boron trifluoride, boron trifluorideetherate, and the like. Such agent is present in catalytic amounts.
This reaction can be carriedv out at pressures above or below atmospheric, but atmospheric pressure is desired to minimize ebullition' of any reaction vehicle and provide an acceptable reaction rate, while maintaining control overv the-reaction. .The temperatures used are in the range of 15 to 120 C., depending upon the catalyst used.
The reaction is suitably carried out in the presence of a vehicle, and solvents for the epoxide and agent are desirable. Such reaction vehicles include aromatic hydrocarbons such as benzene, toluene, xylene, and the like, and benzene is a preferred vehicle. i
Other dihydro derivatives can be produced directly from the pentamethylindane or by isomerization of the 4, -dihydro derivative described above. Thus, the .pentamethylindane can be treatedwith an alkali metal, desirably lithium, in liquid or gaseous ammonia also to provide the 5,7a-dihydro derivatives. Such treatment is carried out at temperatures of from about -40 C. to about 25 C. At the lower temperature atmosperic or slightly subatmospheric pressures can be used. With liquid ammonia at the higher temperatures, superatmospheric pressures up to about five atmospheres are used. Reaction times of from 15 minutes to four hours can be used.
The conjugated 3a,4 dihydro derivative is produced from the non-conjugated material by treatment with an alkali metal, preferably lithium, in an alkylamine, desirably a lower alkylamine such as ethylamine and the like. While it can be conducted at subor superatmospheric pressures, the reaction is desirably carried out at atmospheric pressures. Temperatures of to 17 C. are used, and the time is from 30 minutes to four hours.
The hydrocarbons produced according to'the above reaction schemes can be separated from the vehicle and any unreacted materials or unwanted by-pr'oducts rcmoved by conventional means including washing, distillation, extraction, preparative chromatography, and the like. It is preferred to fractionally distill the washed reaction product under a relatively high vacuum so as to obtain a pure product. Product purities of 80% vare readily obtained, and much higher purities can also be provided by suitable treatment. All parts, proportions, percentages and ratios herein are by Weight unless otherwise indicated.
The dihydropentamethylindanes of this invention are useful as fragrances. They can be used to contribute a woody amber fragrance. As olfactory agents the indane derivatives of this invention can be formulated into or used as components of a perfume composition.
The term perfume composition is used herein to mean a mixture of organic compounds, including, for example, alcohols, aldehydes, ketones, esters, and frequently hydrocarbons which are admixed so that the combined'odors of the individual components produce a pleasant'or desired fragrance. Such perfume compositions ii'sually "contain: (a) the main note. or the bouquet or foundationstone of the composition; (b) modifiers which round-01f and accompany the main note; (0) fixativeswhich include odorous substances which lend a particular note to the perfume throughout all stages of evaporation, and substances which retard evaporation; and (d) top-notes which are usually low-boiling fresh-smelling materials.
In perfume compositions the individual component will contribute its particular olfactory characteristics, but the overall effect of the perfume composition will be the sum of the effect of each ingredient. Thus, the individual compounds of this invention, or mixtures thereof, can
be to alter the aroma characteristics of a perfume composition, for example, by highlighting -or 'moderatnig considerations of cost, nature of the end'produ'ct, the
effect desired on the finished product and the particular fragrance sought. i i
The indane derivatives of this invention can be used alone or in a perfumecomposition as an olfactory component in detergents and soaps; space deodorants; perfumes; colognes; bath preparations such as bath oil-and bath salts; hair preparations such as lacquers, brilliantines, pomades, and shampoosg cosmetic preparations such as creams, deodorants, hand lotions, and sun screens; powders such as talcs, dusting powders, face powder, and the like. When used as an olfactory component of a perfumed article, as little as'0.011% of the novel hydrocarbon will suffice to impart a fine woody amber odor. I In addition, the perfume composition can contain, a vehicle or carrier for the other ingredients. The vehicle can be a liquid such as alcohol, glycol, or the like. The carrier can be an absorbent solid such as a gum or components for encapsulating the composition. i
It will be appreciated that the pentamethylindane derivatives according to this invention can be used to enhance, modify, or supplement the fragrance properties of natural or synthetic fragrance compositions. Thus, such preferred dihydroindanes can be used in fragrance compositions .for addition to perfume compositions or directly to products such as soap, detergents, cosmetics, and the like. The fragrance compositions so prepared do not entirely provide the olfactory properties to the finished perfume or other article, but they, do furnish a substantial part of the overallfragrance impression. The following examples'are given to illustrateembodiments of theinvention as itis presently preferred to prae tice it. It will be understood that these'examples are illustrative, and the invention is not to be considered as restricted thereto except as indicated in ,the'appended claims. EXAMPLE I H v 7 Preparation of 4,5,6,7-tetrahydro-.1,1',2,3,3-pentamethylindane and hexahydro-l,1,2,3,3-pentamethylindane The following ingredients are charged into a stainless steel five-liter autoclave equipped with a hydrogen gas feed:
1,800 g. (8.14 moles) of 1 ,1,2,3,3-pentamethylindane pure) i g. of Raney nickel;
Enough hydrogen is fed into the autoclave to raise the pressure to 1,000 p.s.i.-g. The hydrogen feed is continuous until two moles of hydrogen are absorbed, and:the' auto.- clave is heated to a temperature in the range-of -185 9 C. over a period of about 8 hours until an amount of. H equalv to 10% in excess of theory is absorbed. During this time the pressure in the autoclave is maintained at 1,500 p.s.i.g.
The 1,641 g. of crude product removed from the autoe clave is distilled on a 12-inch Goodloe column after being mixed with 10.0 g. of Primol mineral oil. The distillate is recovered in two fractions.
Fraction 1: Distills at a temperature of 80 C. and 4.0 mm. Hg to provide 401 g. of 4,5,6,7-tetrahydro-1,1,2,3,3- pentamethylindane.
Fraction II is further refined in a similar manner and analysis confirms the structure:
EXAMPLE II (a) Production of 3a,7a-epoxyhexahydro-1,1,2,3,3-
' pentamethylindane Into a 250-ml. flask equipped with thermometer, stirrer, reflux condenser and ice bath are introduced 194 g. of the tetrahydroindane produced in Example I and 15 g. of sodium acetate. At 25-30 C., 124 g. of 40% peracetic acid (0.65 mole) is added during four hours. After addition is completed, an equal volume of water is added to the reaction mass. The aqueous phase is separated from the organic phase and extracted with 150 ml. of toluene. The toluene extract is combined with the organic phase and washed with one volume of 5% aqueous sodium hydroxide solution and then with one volume of water.
The solvent is stripped off leaving a crude product weighing 208 g. The crude epoxy product is distilled on.,.,
a 12-inch Goodloe column after addition of 4.0 g. of triethanolamine at 72-74 C. and 1.01.4 mm. Hg. PMR and IR analysis of this material confirm the structure:
(b) Production of 4,5-dihydro-l,l,2,3,3- pentamethylindane one volume of a 5% sodium chloride solution and dried over anhydrous sodium sulfate. The resulting product is separated on a gas-liquid chromatographic (GLC) column and the various separated constituents are analyzed by PMR, mass, infrared and UV absorption spectroscopy. These analyses confirm the identity of 4,5-dihydro-1,1,2, 3,3-pentamethylindane having the structure:
This material has a fine woody, amber-tobacco aroma. with an elegant piney note.
6 EXAMPLE 1n Preparation of soap composition A total of g. of soap chips (from a toilet soap prepared from tallow and coconut oil) is mixed with one gram of the perfume composition given below until a substantially homogeneous composition is obtained. The soap composition manifests a characteristic woody-amber odor with piney overtones.
The perfume composition comprises the following ingredients:
Ingredient: Parts Vetivert oil 40 Dihydropentamethylindane produced in Example II 60 Sandalwood oil 100 Rose Geranium oil 200 Musk extract (3%) 25 Civet extract (3%) 25 Benzyl iso-eugenol 100 Coumarin 100 Heliotropin 50 Bois de Rose oil 200 Benzoin resin 100 EXAMPLE IV Preparation of a detergent composition A total of 100 grams of a detergent powder is mixed with 0.15 gram of the perfume composition as set forth in Example III until a substantially homogeneous composition having a woody-amber odor is obtained.
EXAMPLE V Preparation of a cosmetic powder composition A cosmetic powder is prepared by mixing 100 grams of talcum powder with 0.25 gram of the dihydroindane obtained from the process of Example H in a ball mill. The cosmetic powder has a desirable woody-amber odor.
EXAMPLE VI Liquid detergent Concentrated liquid detergents with a woody-amber, piney odor are prepared containing 0.1%, 0.15%, and 0.20% of the dihydroindane produced in Example II. They are prepared b adding and homogeneously mixing the appropriate quantity of the compound to Ultra Chemical Companys P-87 liquid detergent.
EXAMPLE VII A 100-ml. reaction flask is fitted with a mechanical stirrer, condenser, and thermometer, and 2.5 g. of hexahydropentamethylindane as produced in Example I and 2.5 g. of palladium on carbon catalyst containing 10% palladium are charged to the flask. The flask contents are brought to 234 C. and refluxed at that temperature for two hours until no further reaction is evident.
The catalyst is then filtered off and the filtrate is analyzed. The product obtained is largely l,1,2,3,3-pentamethylindane.
EXAMPLE VIII 1,1,2,3,3 pentamethylindane is treated with lithium in ammonia for thirty minutes at 33 C. The product is analyzed and found to contain 5,7a-dihydro-1,1,2,3,3- pentamethylindane. The dihydroindane so produced has an amber woody fragrance character suitable for incorporation into perfume compositions such as that set forth in Example 111.
EXAMPLE IX An aliquot of the dihydroindane derivative produced in Example VIII is treated by dissolving lithium in ethylamine until the blue color disappears from the mass and then adding the dihydro material with stirring and continuing the stirring under reflux for one hour.
The ethylamine is evaporated, water is added, and the aqueous mixture is extracted with hexane. The product is found to contain 321,4 dihydro 1,1,2,3,3 penta-rnethylindane. This has an amber woody fragrance character suitable for incorporation into perfume compositions such as that set forth in Example III.
Whatis claimed is:
1. A perfume composition containing as anessential ingredient a fragrance imparting amount of at least one indane derivative selected from the group consisting of 5,7a dihydro 1,1,2,3,3 pentarnethylindane; '3a, 4-dihydro 1,1,2,3,3 pentamethylindane; 4,5,6,' l'- tetrahy- 8 dro-l,1,2,3,3-pentamethylindane; and .hexahydro-1,l,2,3, 3-pentamethylindane and an auxiliary perfume ingredient.
3,183,249 "5/1965 Wiese 260-666'PY 3,681,464 8/1972 Theimer' 252522 19 ALBERT T. MEYERS, Primary Examiner A. P. FAGELSON, Assistant Examiner US. Cl. X.R. 424-69
US00286994A 1969-08-18 1972-09-07 Perfume composition containing hydrogenated indane derivative Expired - Lifetime US3806472A (en)

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US00851049A US3773836A (en) 1969-08-18 1969-08-18 Indanone derivatives and processes for producing same
US851086A US3636176A (en) 1969-08-18 1969-08-18 Hydrogenated indane derivatives and processes for producing same
US851090A US3647826A (en) 1969-08-18 1969-08-18 Indane derivatives
US851048A US3681464A (en) 1969-08-18 1969-08-18 Saturated indane derivatives and processes for producing same
US851076A US3636165A (en) 1969-08-18 1969-08-18 Indanol derivatives and processes for producing same
US00286994A US3806472A (en) 1969-08-18 1972-09-07 Perfume composition containing hydrogenated indane derivative

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US85104869A 1969-08-18 1969-08-18
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US85107669A 1969-08-18 1969-08-18
US85104969A 1969-08-18 1969-08-18
US11583471A 1971-02-16 1971-02-16
US18464071A 1971-09-28 1971-09-28
US00286994A US3806472A (en) 1969-08-18 1972-09-07 Perfume composition containing hydrogenated indane derivative
US00325676A US3839368A (en) 1969-08-18 1973-01-22 7,7a-epoxy-5,6,7,7a-tetrahydro-1,1,2,3,3-pentamethyl-4(3ah)-indanone
US00325677A US3816350A (en) 1969-08-18 1973-01-22 Perfume composition containing indanone derivatives

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US851076A Expired - Lifetime US3636165A (en) 1969-08-18 1969-08-18 Indanol derivatives and processes for producing same
US00851049A Expired - Lifetime US3773836A (en) 1969-08-18 1969-08-18 Indanone derivatives and processes for producing same
US851086A Expired - Lifetime US3636176A (en) 1969-08-18 1969-08-18 Hydrogenated indane derivatives and processes for producing same
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US6303798B1 (en) 2001-02-23 2001-10-16 International Flavors & Fragrances Inc. Methylene dioxy tetrahydroindane derivative
US20050009729A1 (en) * 2003-07-10 2005-01-13 Monteleone Michael G. Acetonide fragrance compound
US7115553B2 (en) 2003-07-10 2006-10-03 International Flavors & Fragrances Inc. Acetonide fragrance compound
CN100582099C (en) * 2003-11-28 2010-01-20 弗门尼舍有限公司 Musk odorant compound

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US3681464A (en) 1972-08-01
US3773836A (en) 1973-11-20
US3636176A (en) 1972-01-18
US3636165A (en) 1972-01-18
US3647826A (en) 1972-03-07

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